(R)-(-)-2-ethyloctan-1-ol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-(-)-2-ethyloctan-1-ol
• 英文别名: (-)-2-ethyloctan-1-ol；(2R)-ethyl-1-octanol；(2R)-2-ethyloctan-1-ol
• 化学式: C₁₀H₂₂O
• 分子量: 158.284
• InChiKey: HTRVTKUOKQWGMO-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-(-)-2-ethyloctan-1-ol 在 吡啶 、 2,6-二甲基吡啶 、 potassium carbonate 、 氯甲酸苯酯 、 sodium iodide 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 54.0h， 生成 (R)-phenyl 2-ethyloctyl(phenyl)carbamate
  参考文献：
  名称：

  金属催化不对称碳-碳键形成过程的新导向基团：未活化亲电试剂的立体聚合烷基-烷基铃木交叉偶联

  摘要：

  两种常见受保护形式的胺（氨基甲酸酯和磺酰胺）在 Ni 催化的 Suzuki 反应中作为导向基团的能力已被用于开发用于交叉偶联未活化烷基亲电子试剂的催化不对称方法。在市售镍配合物和手性配体存在下，外消旋仲溴化物和氯化物在室温下以良好的 ee 立体收敛过程中形成 CC 键。旨在阐明与 Ni（氨基甲酸酯和磺酰胺的氧）结合的位点的结构对映选择性研究导致发现，砜也可用作外消旋烷基卤化物的不对称 Suzuki 交叉偶联的有用导向基团。据我们所知，这项研究提供了在金属催化的不对称 CC 键形成反应中使用磺酰胺或砜作为有效导向基团的第一个例子。一项机理研究表明，金属转移发生时保留了立体化学，并且由此产生的 Ni-C 键在催化循环的后续阶段不会发生均裂。

  DOI：

  10.1021/ja301612y
• 作为产物：
  描述：

  (E)-1-bromo-2-hexene 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 、 lithium diisopropyl amide 作用下， 以 乙醚 为溶剂， 生成 (R)-(-)-2-ethyloctan-1-ol
  参考文献：
  名称：

  Regio- and enantioselective carbolithiation of non-activated CC bonds

  摘要：

  Primary alkyllithiums in the presence of (-)-sparteine, add to terminal conjugated dienes. They also add to 2,4-pentadien-1-ols if they are substituted on C(5), and give rise to allyllithium intermediates, 2-Alkylalkan-1-ols have thus been prepared with ee's up to 74%. (C) 2000 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01091-1

文献信息

• Development of a Merged Conjugate Addition/Oxidative Coupling Sequence. Application to the Enantioselective Total Synthesis of Metacycloprodigiosin and Prodigiosin R1
  作者：Michael D. Clift、Regan J. Thomson

  DOI：10.1021/ja906122g

  日期：2009.10.14

  reagent with subsequent enolate trapping by a (chloro)silylenol ether. The process was applied to the first enantioselective syntheses of the biologically active pyrrolophane natural products, metacycloprodigiosin and prodigiosin R1.

  已开发出一种合并的共轭加成/氧化偶联序列，该序列代表了制备结构多样的吡咯的有效策略。该方法的成功取决于不对称甲硅烷基双烯醇醚中间体的受控氧化偶联，该中间体由格氏试剂的 1,4-加成形成，随后烯醇被（氯）甲硅烷醇醚捕获。该过程被应用于具有生物活性的吡咯烷天然产物、metacycloprodigiosin 和 prodigiosin R1 的第一次对映选择性合成。
• Asymmetric Nickel-Catalyzed Negishi Cross-Couplings of Secondary α-Bromo Amides with Organozinc Reagents
  作者：Christian Fischer、Gregory C. Fu

  DOI：10.1021/ja0506509

  日期：2005.4.1

  A Ni/Pybox catalyst achieves the asymmetric cross-coupling of secondary alpha-bromo amides with organozinc reagents. The process tolerates a variety of functional groups and affords the desired product in good yield and in high enantiomeric excess.

  Ni/Pybox 催化剂实现了仲 α-溴酰胺与有机锌试剂的不对称交叉偶联。该方法耐受多种官能团，并以良好的产率和高对映体过量提供所需的产物。
• Catalytic enantioselective ethylalumination of terminal alkenes: substrate effects and absolute configuration assignment
  作者：Lyudmila V. Parfenova、Pavel V. Kovyazin、Tatyana V. Tyumkina、Alyona V. Makrushina、Leonard M. Khalilov、Usein M. Dzhemilev

  DOI：10.1016/j.tetasy.2014.11.019

  日期：2015.2

  The chemo- and enantioselectivity of the reaction of alkenes with AlEt3 catalyzed by bis(1-neomenthyl-indenyl)zirconium dichloride has been studied. The reaction with linear alkenes in a chlorinated solvent (CH2Cl2) gives mainly carbometallation products in 70-80% yield and with enantiomeric purity of 47-70%ee with an (S)-configuration. In the case of vinylcycloalkanes and styrene, the reaction provides roughly equal amounts of carbometallation products and substituted alumolanes with enantioselectivities of 39-69%ee and 40-57%ee, respectively.(R)-MTPA and (R)-2-phenylselenopropionic acid [(R)-PSPA] were used as the derivatization reagents for enantiomeric excess estimation and the absolute configuration assignment of beta-chiral primary alcohols and 2-substituted 1,4-butanediols resulting from oxidation and hydrolysis of the organoaluminum products. It was shown that the specific rotation changes sign in the series of enantiomerically enriched 2-ethyl-1-alkanols when going from beta-ethyl-substituted octanol to nonanol. The conformational analysis of the MTPA and PSPA esters of 2-ethyl-1-alkanols was performed and a dependence of their conformational composition on the type of substituent at the beta-stereogenic center was established. Calculation of the Se-77 NMR chemical shifts of the possible conformers of the PSPA esters demonstrated that the conformation of the selenium moiety has the most pronounced effect on the delta(Se) value. The high efficiency of PSPA application for the enantiomeric purity estimation and the absolute configuration assignment of 2-ethyl-1-alkanols is shown. (C) 2014 Elsevier Ltd. All rights reserved.
• New Directing Groups for Metal-Catalyzed Asymmetric Carbon–Carbon Bond-Forming Processes: Stereoconvergent Alkyl–Alkyl Suzuki Cross-Couplings of Unactivated Electrophiles
  作者：Ashraf Wilsily、Francesco Tramutola、Nathan A. Owston、Gregory C. Fu

  DOI：10.1021/ja301612y

  日期：2012.4.4

  two common protected forms of amines (carbamates and sulfonamides) to serve as directing groups in Ni-catalyzed Suzuki reactions has been exploited in the development of catalytic asymmetric methods for cross-coupling unactivated alkyl electrophiles. Racemic secondary bromides and chlorides undergo C-C bond formation in a stereoconvergent process in good ee at room temperature in the presence of a commercially

  两种常见受保护形式的胺（氨基甲酸酯和磺酰胺）在 Ni 催化的 Suzuki 反应中作为导向基团的能力已被用于开发用于交叉偶联未活化烷基亲电子试剂的催化不对称方法。在市售镍配合物和手性配体存在下，外消旋仲溴化物和氯化物在室温下以良好的 ee 立体收敛过程中形成 CC 键。旨在阐明与 Ni（氨基甲酸酯和磺酰胺的氧）结合的位点的结构对映选择性研究导致发现，砜也可用作外消旋烷基卤化物的不对称 Suzuki 交叉偶联的有用导向基团。据我们所知，这项研究提供了在金属催化的不对称 CC 键形成反应中使用磺酰胺或砜作为有效导向基团的第一个例子。一项机理研究表明，金属转移发生时保留了立体化学，并且由此产生的 Ni-C 键在催化循环的后续阶段不会发生均裂。
• Regio- and enantioselective carbolithiation of non-activated CC bonds
  作者：Stéphanie Norsikian、Monique Baudry、Jean F Normant

  DOI：10.1016/s0040-4039(00)01091-1

  日期：2000.8

  Primary alkyllithiums in the presence of (-)-sparteine, add to terminal conjugated dienes. They also add to 2,4-pentadien-1-ols if they are substituted on C(5), and give rise to allyllithium intermediates, 2-Alkylalkan-1-ols have thus been prepared with ee's up to 74%. (C) 2000 Elsevier Science Ltd, All rights reserved.